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Publication numberUS5116604 A
Publication typeGrant
Application numberUS 07/765,811
Publication dateMay 26, 1992
Filing dateSep 26, 1991
Priority dateJan 16, 1991
Fee statusPaid
Publication number07765811, 765811, US 5116604 A, US 5116604A, US-A-5116604, US5116604 A, US5116604A
InventorsArnold W. Fogel, Albert Zofchak
Original AssigneeBernel Chemical Co., Alzo, Inc.
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Sunscreen compositions containing novel neopentanoate esters
US 5116604 A
Abstract
This invention is concerned with the use of neopentanoate esters as novel cosmetic emollients for sunscreen products.
The use of isoarachidyl neopentanoate in sunscreen formulations offer new and unexpected results over the use of similar esters previously disclosed.
The isoarachidyl neopentanoate has a minimal odor, good stability, water white color, higher sun protection factor values, good emolliency, good crystal solibilization, very low freeze point. It forms the emollient basis for a new way to make very high sun protection factor products.
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Claims(1)
What is claimed is:
1. A sunscreen composition which comprises stearic acid, cetyl alcohol, diethanolamine cetyl phosphate, 100 centistokes silicone fluid, octyl p-methoxy cinnamate, octyl salicylate, deionized water, glycerine, magnesium aluminum silicate, xanthan gum, triethanolamine diethanolamine p-methoxy cinnamate, a preservative, and from 5 to 20% by weight of the composition neopentanoate emollient having the chemical structure as follows: ##STR6## where R1 is a C20 alcohol moiety of the neopentanoate ester having the chemical structure: ##STR7## R2 is the acid moiety of the neopentanote having the chemical structure: ##STR8## which emollient increases the sunscreen protection factor of the composition, stability and pleasant odorific properties due to the emollient's unique stability.
Description

The instant application Ser. No. 07/765,811, filed Sep. 26, 1991 as a continuation-in-part of Ser. No. 07/645,334, filed Jan. 16, 1991, which is a continuation-in-part of application Ser. No. 07/335,439, filed Mar. 20, 1989, both now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to the unique effects and characteristics when novel neopentanoate esters are used in varying concentrations as emollients in conjunction with the active ingredient in sunscreen formulations. The use of the preferred embodiment of this invention, isoarachidyl neopentanoate, offers new and unexpected results from similar esters previously used.

2. Description of Prior Art

U.S. Pat. No. 4,005,210 discloses an emollient for use on the skin which contains isodecyl neopentanoate.

U.S. Pat. No. 4,724,240 discloses the use of carboxylic acid esters as emollients in various types of preparations which include cosmetic and sunscreen applications. It is said that esters which are useful for use as emollients in compositions of this type include esters made from C1 -C30 alcohols and C1 -C30 carboxylic acids. Arachidyl proprionate is mentioned as an example of an ester which can be used in the composition of this patent.

U.S. Pat. No. 4,724,240 discloses the use of a broad range of esters (esters made from C1 -C30 carboxylic acids).

U.S. Pat. No. 4,724,240 specifies the use of arachididyl proprionate for use as an emollient and U.S. Pat. No. 4,005,210 discloses the use of isodecyl neopentanoate as an emollient.

There have been other uses of fatty acid esters as emollients in cosmetic and sunscreen formulations.

OBJECTS AND SUMMARY OF INVENTION

It is the object of this invention to provide novel neopentanoate esters as emollients having unique properties making these esters uniquely suitable in sunscreen formulations.

It is the further object of this invention to provide varying percentages of these unique neopentanoate esters as emollients in sunscreen formulations.

It is believed that the uniqueness of these emollients is due to the reaction of neopentanoic acid and the specific alcohols used [Exxals by Exxon].

These novel neopentanoates exhibit properties unlike other similar esters currently used as emollients. It is these properties, e.g:

(1) Unusual low odor

(2) Good stability at 50° C. for over 3 months

(3) Water white color

(4) Higher SPF values

(5) Good emolliency (light with low residuals)

(6) Good crystal solubilizers

(7) Very low freeze points

(8) Non hydrolyzable in acid pH emulsions

(9) Negative comedogenicity

These unique unexpected properties are the focal point of the present invention. The sunscreen products formulated with the instant invention have an unexpected high SPF value.

The preferred embodiment of this invention is Isoarachidyl Neopentanoate formed by reaction of a C20 alcohol with neopentanoic acid having the following structure: ##STR1##

DETAILED DESCRIPTION OF THE INVENTION

The use of esters as emollients in cosmetic and sunscreen formulations are well known. They are found by the reaction of an organic acid and an alcohol. ##STR2## where R1 may be: ##STR3## and R2 is ##STR4##

In the instant invention, the preferred embodiment is formed as follows: ##STR5##

The use of isoarachidyl neopentanoate, the preferred embodiment of the invention, results in products with low odor, good stability and higher S P F values. The isoarachidyl neopentanoate is a clear, water white liquid, has good emolliency and is a good crystal solubilizer when comprising 5%-20% by weight of the sunscreen formulation. It is an extraordinary, silky, unusual emollient which exhibits greater "slip" and significantly enhances the Sun Screen Protective Factor ("S P F"), the isoarachidyl neopentanoate is a low freezing liquid, non-comedogenic, stable and safe.

The isoarachidyl neopentanoate in formulations remains odorless after a minimum of three months storage at 50° C. The fact that it is water white, stable and odorless are unique and novel characteristics of this invention.

These unique properties make the isoarchidyl neopentonoate the preferred emollient in sunscreen formulations.

The C16, C18 and C26 neopentanoates which have also been made using specific alcohols [Exxals by Exxon] for use as sunscreen emollients also exhibit significantly enhanced properties over the present art. However, superior results in sunscreen formulations are obtained when using the preferred embodiment of the invention, isoarachidyl neopentanoate, as the emollient moiety.

Following on the next page are the description and test results of the preferred embodiment of the invention using 10% Elefac, the instant invention in sunscreen formulation F-4-6-2, F-4-8-1, F-4-10-1 and F-4-14,

EXAMPLES The Formulations

Formula F-4-6-2--Uses 7.5% Parsol MCX and 2% Oxybenzone. We normally would expect an SPF of 18 (on 20 people). We wanted to score the highest SPF possible while keeping the Oxybenzone at a maximum 2% level, with Parsol MCX as the only other U.V. absorber.

Formula F-4-8-1--We were going for maximum SPF with 3 screens, i.e.: Parsol MCX at 7.5% oxybenzone at 6.0% and Octyl Salicylate at 5%. With Bernel Ester DOM in this emulsion, we scored an SPF of 27 (on 20 people), whereas, using 10% Elefac I-205 to replace the "DOM" we scored and SSPF of 34 (on 20 people).

Formula F-4-10-1--We wanted a PABA and PABA Ester free, as well as a Benzophenone free emulsion to give an SPF 15 or above. We scored an SPF of 24 (on 7 people) when we only expected an approximate, SPF of 16-18. Used alone, 7.5% "MCX" yields an SPF of 8 (app.) and 7.5% Hydro, (used alone) also yields an SPF of 8 (app.). When used together, with 10% elefac I-205 added, we scored an SPF of 24.

Formula F-4-14-1--We added 5% Octyl Salicylate and 0.3%, Sodium Metabisulfite to formula F-4-10-1 expecting an SPF of 30 (app.). We scored 35/28 (on 20 people) and again PABA free and Oxybenzone free.

All formulations are "PABA and PABA Ester" free. All score an SPF 15 and above. Some are "Benzophenone" free also.

The Exxal 20 alcohol is the specific alcohol used in manufacturing the neopentanoate emollient used in all the foregoing formulations.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US4005210 *Jul 3, 1975Jan 25, 1977Estee Lauder, Inc.Protein containing emollient composition for a skin moisturizer
US4663155 *Feb 19, 1985May 5, 1987Johnson & Johnson Baby Products CompanySunscreen compositions
US4699781 *Mar 2, 1987Oct 13, 1987Goupil Jean JacquesSun products
US4724240 *Dec 12, 1984Feb 9, 1988Wickhen Products, Inc.Lattice-entrapped emollient-moisturizer composition
Non-Patent Citations
Reference
1 *AMA Laboratories Bernel Chem. Co., Table 1 Feb. 1, 1989.
2 *AMA Laboratories Summary Sheet, Dec. 22, 1988, Cantor.
3 *AMA Laboratories, Summary Sheet, Dec. 12, 1988, Cantor.
4 *AMA Laboratories, Summary Sheet, Nov. 1988, Bernel Chemical Co., Inc.
5 *AMA Laboratories, Table 1, Nov. 1988, Bernel Chemical Co. Inc.
6 *Exxon Chemical Exxal 20 Iso Arachidylalcohol Data Sheet, Jun. 16, 1988, pp. 1 to 7.
7Exxon Chemical Exxal 20-Iso Arachidylalcohol Data Sheet, Jun. 16, 1988, pp. 1 to 7.
8 *Product Identification, Exxal 20 Isoarachidyl Alcohol Jun. 16, 1988 pp. 1 to 4.
9Product Identification, Exxal 20-Isoarachidyl Alcohol Jun. 16, 1988 pp. 1 to 4.
10 *Table I, AMALAB, Bernel Chemical, Feb. 1989, p. 1.
11 *Technical Bulletin & Summary Sheet, Feb. 1989, SPF34/28, pp. 1 and 2.
12 *Technical Bulletin, Feb. 1989, Suntan Cream SPF34/28.
13 *Technical Bulletin, Feb. 1989, Suntan Lotion SPF18 AMA Laboratories, Summary Sheet, Feb. 1, 1989, Cantor.
14 *Technical Bulletin, Jan. 1989, Suntan Cream SPF24.
15 *Technical Bulletin, Jan. 1989, Suntan Cream, SPF34.
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5476643 *Nov 19, 1993Dec 19, 1995Bernel Chemical Co.Method of dispersing micronized TIo2, ZnO and other pigments
US5476648 *Mar 12, 1993Dec 19, 1995Bernel ChemicalOil in water emulsions
US5498406 *Apr 30, 1993Mar 12, 1996Nearn; Malcolm R.Titanium dioxide-based sunscreen compositions
US5620682 *Mar 25, 1993Apr 15, 1997Bernel Chemical Co.Sunscreen compositions
US5707612 *Apr 8, 1996Jan 13, 1998Alzo, Inc.Use urethane polymers of castor oil skin and personal care product compositiions
US5716602 *Jun 26, 1996Feb 10, 1998S. C. Johnson & Sons, Inc.Insect repellent sunscreen
US5738841 *Jan 26, 1996Apr 14, 1998L'orealCosmetic composition comprising a silicone-containing compound and a fatty acid ester
US5783173 *Nov 21, 1996Jul 21, 1998The C. P. Hall CompanyStable sunscreen composition containing dibenzoylmethane derivative, E. G., PARSOL 1789, and C12, C16, C18, branched chain hydroxybenzoate and/or C12, C16, branched chain benzoate stabilizers/solubilizers
US5788954 *Nov 12, 1997Aug 4, 1998The C. P. Hall CompanyHydrating skin care and sunscreen composition containing dibenzoylmethane derivative, E.G., parsol 1789, and C12, C16, C18 branched chain hydroxybenzoate and/or C12, C16, branched chain benzoate stabilizers/solubilizers
US5849273 *Dec 4, 1997Dec 15, 1998The C. P. Hall CompanySkin care and sunscreen composition containing dibenzoylmethane derivative, e.g., parsol® 1789, and C12, C16, C18 branched chain hydroxybenzoate and/or C12, C16 branched chain benzoate stabilizers/solubilizers
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US20090185984 *Oct 12, 2006Jul 23, 2009Sensient Colors Inc.Colorants surface treated with urethanes and methods for making and using the same
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Classifications
U.S. Classification424/59, 424/60, 514/873
International ClassificationA61Q17/04, A61K8/37
Cooperative ClassificationY10S514/873, A61Q17/04, A61K8/37
European ClassificationA61Q17/04, A61K8/37
Legal Events
DateCodeEventDescription
Sep 26, 1991ASAssignment
Owner name: BERNEL CHEMICAL COMPANY
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:FOGEL, ARNOLD W.;ZOFCHAK, ALBERT;REEL/FRAME:005851/0908
Effective date: 19910729
Owner name: ALZO, INC., NEW JERSEY
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:FOGEL, ARNOLD W.;ZOFCHAK, ALBERT;REEL/FRAME:005851/0908
Effective date: 19910729
Jan 2, 1996REMIMaintenance fee reminder mailed
May 26, 1996REINReinstatement after maintenance fee payment confirmed
Aug 6, 1996FPExpired due to failure to pay maintenance fee
Effective date: 19960529
Mar 18, 1998SULPSurcharge for late payment
Mar 18, 1998FPAYFee payment
Year of fee payment: 4
Sep 22, 1998PRDPPatent reinstated due to the acceptance of a late maintenance fee
Effective date: 19980717
Feb 8, 2000FPAYFee payment
Year of fee payment: 8
Feb 8, 2000SULPSurcharge for late payment
Mar 9, 2000ASAssignment
Owner name: FLEET BANK, NATIONAL ASSOCIATION, NEW JERSEY
Free format text: SECURITY AGREEMENT;ASSIGNOR:ALZO INTERNATIONAL, INC. (FORMERLY ALZO, INC.);REEL/FRAME:010668/0290
Effective date: 20000303
Oct 17, 2003FPAYFee payment
Year of fee payment: 12